Chloroacetyl chloride → HCID 22316553, compound

HRID 1058894Notes

Reaction equation

HRID 1058894 reaction equation
[NH2:1][C:2]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:13])=[O:5].[Cl:21][CH2:22][C:23](Cl)=O>C(O)(=O)C>[Cl:21][CH2:22][C:23]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[C:4](=[O:5])[C:3]2[C:2](=[CH:17][C:16]([N+:18]([O-:20])=[O:19])=[CH:15][CH:14]=2)[N:1]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 22316574HCID 22316574, compound

Product 1

HCID 22316553HCID 22316553, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Prepared according to Procedure B with 1o (500 mg, 1.71 mmol) and chloroacetyl chloride (0.41 mL, 5.14 mmol) in acetic acid (10 mL). Purified by extraction from aqueous K2CO3, followed by two chromatographies in CH2Cl2 to afford 338 mg of a yellow oil (56%). 1H NMR (CDCl3) δ: 8.64 (d, J=2.2 Hz, 1H); 8.48 (d, J=8.8 Hz, 1H); 8.32 (dd, J=2.2, 8.7 Hz, 1H); 7.66 (dd, J=2.5, 6.0 Hz, 1H); 7.52-7.59 (m, 3H); 4.41 (d, J=12 Hz, 1H), 4.10 (d, J=12 Hz, 1H). MS (ES): m/z 350.0 (M+)

Workup

  1. customPrepared
  2. customPurified by extraction from aqueous K2CO3

Sources & evidence

ORD record
ord-09e42dcefdba41318d54c6b921b6292e
Source dataset
uspto-grants-2003_02
Patent number
US06518277B1

Reaction notes

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